Product Rising Navigating Leadership with Confidence and Curiosity with Bosky Mukherjee
In this episode, Cassie welcomes Bosky Mukherjee, the prolific founder of PM Dojo and SheTrailblazes, and a veteran product advisor, leadership coach, and trainer. Bosky discusses her journey into product leadership, the formation of PM Dojo, and her mission to support women in product management. The conversation delves into the nuances of product management training versus coaching, the impact of AI on the industry, and strategies for driving cultural shifts within organizations. Bosky also shares insights on balancing humility with confidence and offers practical advice on leveraging coaching to unlock business potential and personal growth.
More about Bosky:
Bosky Mukherjee, an executive tech leader with over 22 years of global experience—spanning early-stage startups to high-growth companies like Atlassian.
She’s the founder of SheTrailblazes and a powerful force for change in how women succeed, thrive, and rise to the top. Through her flagship program, Leadership Edge, Bosky equips women to lead with strategic visibility and executive communication—fast-tracking their path to promotion, all the way to the C-suite, and when the time is right, into entrepreneurship.
Her work isn’t just about career growth. It’s about power, parity, and making sure women aren’t just at the table—but driving the agenda.
Bosky is also the founder of PMDojo, where she helps companies build stronger, more strategic innovation teams—equipping product and technology talent to drive bigger business impact and communicate with executive fluency.
00:00 Introduction and Guest Welcome
00:49 Bosky's Journey into Product Leadership
01:36 Challenges and Realizations in the Executive Room
03:05 Founding PM Dojo and Its Mission
04:50 AI in Product Management
09:41 Training vs. Product Leadership Coaching
11:05 Coaching Styles and Skills Development
15:03 Working with Companies and Teams
18:56 Driving Cultural Shifts in Organizations
23:19 Assigning Dollar Value to Business Transformation
23:33 Navigating Product Leadership Challenges
24:38 Implementing Small Shifts for Big Changes
25:25 Facilitating Business Conversations
26:47 Success Stories and Skill Development
28:39 Working It Out: Lessons from School
30:26 Confidence, Humility, and Curiosity
31:55 Hiring a Coach: When and Why
34:53 Building Community and Networking
38:18 Creative Budget Solutions for Product Teams
44:10 Conclusion and Final Thoughts
📚Resources:
✨Where to find Bosky Mukherjee:
💫 Where to find Cassie:
At Cassie Camp - Learn more about product leadership coaching and fractional product leadership
🙋🏻♀️Where to find Women in Product:
Website https://womenpm.org/
Join the Community https://womenpm.org/wip-community/